Swesson Collection
by WrenClayton
Summary: Drabbles of Dean Smith and Sam Wesson having naughty times in the office. Four drabbles, four kinks. Contains pay-raise-in-exchange-for-sex, phonesex, mentions of crossdressing, almost-public sex, and dom/sub.
1. Chapter 1

"Yeah, yeah, I've already dealt with Robertson, she's in."

Dean Smith scribbled a note as he spoke into the earpiece, sitting at his desk. "Yeah. Yesterday. … What?" He straightened up. "What the hell do you mean she's backing out?" Dean listened to the voice on the other end for a few moments, then let out an irritated grunt and muted his own sound input. He glared under the desk at the man who was sitting naked on his knees, pretty pink lips wrapped around Dean's cock.

"Keep sucking, you want that pay raise or not?"

Sam Wesson nodded, pumping his mouth up and down his boss's cock. Dean gave a little grunt of pleasure and turned his earpiece back on.

"Okay, tell George to call up Robertson right now and tell her I've got dirt on her. Yes, tell her _I've _got dirt on her. Me, Dean Smith. She'll know what I'm talking about. Tell her that." Dean clicked the earpiece off and reached under the table to tangle his fingers in Sam Wesson's hair.

"You're not bad at this," he grunted, biting his lip when Sam's lips dragged up his shaft, sucking all the way. "Mmf… you keep this up and I might just offer you another pay raise to do this again tomorrow."

Sam tried to nod again, looking up at his boss obediently as he sucked.

Dean bit his lip, starting to grin. His hand tightened in Sam's hair and he started guiding Sam's movements, thrusting into that mouth. "Here's what I'm thinking. I'm thinking if you want more than just a little pay raise, you'll start fingering your tight ass for me."

Sam gave a little whimper around Dean's cock, but reached between his legs all the same. He groaned when he slid a finger in.

Dean's ear piece was buzzing again. He mouthed the command "_thrust_" before clicking it on. "Yes, this is Dean Smith? Robertson's on board? Thought she might be."


	2. Phone Sex

Sam Wesson was actually relieved when the phone rang. He'd been clicking and dragging digital reports for what felt like hours. He brought the phone up to his ear and leaned back in his wheelie chair with a sigh. "Tech support, this is Sam Wesson, how may I help you?"

"It's your boss, sugar-butt, put on your bedroom voice."

Sam's face went red and he glanced around to make sure no one saw. He cleared his throat and tried to speak normally. "Wh-what can I do for you, sir?"

He could hear Dean Smith chuckling over the phone. His voice was low and hungry. "For starters, you can tell me what you're wearing."

Sam pursed his eyebrows. " … Uh… company uniform, sir." He glanced around another time, hoping no one was piecing together what Mr. Smith had asked him.

Dean Smith gave an impatient sigh. "All right, let's try this again. What _should_you be wearing?"

Sam's breath caught. " … Nothing," he choked out.

"Yeah, that's more like it." He could hear a little grunt from the other end of the phone. "But I bet you can do even better."

Sam gave the room one more anxious glance before opening a new tab on his computer and going to a site he really ought to not be looking at during work hours. "I'm emailing the file to you right now, sir," he said professionally, dragging an image onto his desktop and then onto an email.

"Oh, are you?"

Sam clicked "send," and heard a beep from the other end of the phone. It was followed by a groan.

"Mmm, _much_ better, Wesson. Nice and… frilly. Your ass would look great in that while I'm fucking it."

Sam's breath hitched and he dragged another image onto his desktop. "Sending more files, sir."

He attached an image of a leather collar and a buttplug before closing all the windows and palming his erection through his pants, waiting breathless for his boss's response.


	3. Elevator Quickie

Sam Wesson was tense as he walked towards the elevator, hoping no one would glance down and see the hard-on raging in his pants. He could still hear his boss's low voice, whispering to him through the phone.

_"I want you to get that sweet ass on elevator three in exactly five minutes, sugar-butt. Got it?"_

Sam tapped his foot nervously as the elevator light clicked down, one floor at a time. He'd been palming himself through his pants for a good half an hour, talking to his boss on the phone. Wishing he could finger himself while he listened to his boss talk about bending Sam over his desk and working his nice thick cock into Sam's ass, pumping it in and out…

Sam glanced around and gave his cock another squeeze. It jumped against his hand. He was right on the fucking _edge_ of coming in his pants, his whole body was shivering. The elevator finally dinged and Sam almost groaned when it opened and revealed Dean Smith, all suit and combed hair and authority. He gave Sam a brief glance as if just noticing him and said, "Morning."

Sam ducked his head, swallowing. "Morning, sir." He got on the elevator quickly, practically slamming his hand against the button for the top floor. The instant the doors slid shut, he was being shoved against the wall and kissed ravenously.

"Fucking hell, Wesson," Dean Smith panted into the kiss, already ripping Sam's pants open. "That picture you sent me? The panties? I'm buying you some." He pulled Sam's cock out of his pants and started jacking it off, making Sam's whole body buck. "Gonna make you wear it around work."

"F-fuck!" Sam thrust into his boss's hand, grabbing his hair and kissing him hard. The elevator dinged as it passed a floor.

"Gonna get me so fucking hard, sitting at my desk thinking about you doing your work with those black lacy panties wrapped around your cock and balls… "

Sam panted as Dean dropped to his knees, kissing the head of his cock. "Said you weren't gonna take 'em off when you fucked me," Sam choked out, watching his boss lick over his twitching erection. "Said you were just gonna pull 'em aside and shove your dick in." Sam's head thumped back against the elevator wall when he was sucked into Dean's mouth. The elevator dinged past another floor. "I could walk up to your office wearing my work clothes and when you rip 'em off have those panties waiting for you — _fuck_ — "

Dean yanked Sam's pants down as he blew his employee, sucking the throbbing head. He grabbed Sam's round ass in his hands and squeezed.

Sam was gasping, grabbing Dean's shoulders so as not to mess up his hair. "Wanted your cock in me so badly today, god, you've got no idea, couldn't f-fucking stand it — " Sam groaned loudly and thumped his fists against the wall as Dean pushed a finger into his tight hole. "Oh fuck yes, god, yes… "

Dean pumped the finger in and out, sucking Sam so hard he thought he would black out. Sam shouted and cursed as he came in his boss's mouth, feeling Dean gulp it all down, tightening around that finger. He was still panting when Dean stood up and started working his own pants open.

"Turn around," Dean hissed.

Sam faced the wall and pulled his pants down farther, grabbing his ass and spreading it invitingly. Dean groaned and pulled a packet of lube out of his pocket, squeezing the cool, slick liquid over Sam's hole. "Won't take long," he panted. "Not after the teasing you gave me, fuck… "

Sam glared over his shoulder. "You're the one who called my cubicle," he hissed.

Dean groaned and slotted his cock in Sam's ass, pressing the cheeks together and humping. "God, fuck… You've just got the roundest, plumpest ass, Wesson… "

Sam pushed his hips back against his boss's, giving Dean something to thrust against. He could feel the slick slide of Dean's cock over his hole. He closed his eyes and thought about how that dick felt when it was pulsing, coming, squirting hot and wet and slippery all over his tight little hole —

"Fuck, fuck, gonna come… " Dean grabbed Sam's hips and thrust hard, sliding his dick through that warm crack. He pulled back a few inches, pushing the head of his cock against Sam's hole, and Sam's eyes snapped open. "Gotta come inside that sweet ass, can't leave a mess."

Dean's hand closed over Sam's mouth, muffling his shout as Dean pushed into him, stretching his tight hole. Dean groaned into Sam's neck and thrust his hips forward once, and Sam shuddered and gasped as he felt Dean's come gushing inside him.

"Ffffffuck, yes… " Dean let out a tense breath and gave the back of Sam's neck a kiss. "You always deliver, Wesson."

Sam was just letting out a content sigh when a ding from the elevator reminded him where they were.

"Shit!" He pulled himself off of Dean's cock, yanking his pants back up. Dean wrestled with his own pants, and they each took a second to neaten their hair and clothes and put on a poker face just in time for the the elevator doors to slide open. A man in a suit glanced over them, and gave Dean a smile.

"Morning, Mr. Smith."

Dean gave him a nod. "Morning." He walked out of the elevator without a glance back at Sam. Sam blew out a breath as the man stepped in next to him, and tried his damnedest to not act as if he had his boss's come in his ass as the elevator started dinging its way back down.


	4. Dom Sam

Dean Smith happened to glance at the clock, and almost jumped when he saw it was twelve fifty-seven. He grabbed the phone frantically. He would have been in trouble if he'd called late.

Dean quickly dialed and let out a tense huff, listening to the ring and chewing his lip. His heart was racing with nerves and eagerness. Almost late. God. Just the thought of it sent a jolt of excitement through him.

There was a click, then a voice on the other end of the line. "Hello, tech support, this is Sam Wesson."

Dean Smith swallowed and found his steady business voice. "Sam Wesson, this is Dean Smith. I need to see you in my office to discuss report number forty."

"Right away, sir. I'll be there in two minutes." The phone clicked off.

Dean glanced at the clock as he hung up. Twelve fifty-eight. Cutting it close. He stood up and locked the door, closed the blinds, disabled the bugs in his office, and stripped out of his shirt. He reattached his tie, though. Sam liked to tug on it.

There was a knock on his door, and Dean responded by calling the words he always called. "I'm very busy, is it important?"

"I'm here to discuss report number forty, sir," came Sam Wesson's voice.

Dean swallowed and unlocked the door, hiding behind it as he cracked it open. Sam Wesson stepped inside, not looking at him, and Dean quickly shut the door and locked it again. As soon as it was latched, he dropped to his knees and held his hands behind his back, looking up at Sam.

Sam was looking at his watch. "Exactly twelve." He gave Dean a warning look. "You came very close to missing our date."

"I'm sorry, Master." Dean held his position, heart pounding.

Sam walked up to Dean and ran his hand through his boss's hair, destroying the perfect combing. "You'll have to start making it up to me," he whispered.

Dean just opened his mouth, letting his tongue hang out as Sam continued to pet him. Sam smirked, starting to undo his pants. "That's a good bitch."


End file.
